Schools are important environments for promotion of healthy behaviors to reduce childhood obesity; however, many barriers prevent schools from sustaining wellness programs. The goal of the Healthy Champions program was to assist schools with identifying areas for improvement through a nutrition and activity-focused assessment, and delivery of a customized score report and welcome kit with materials to promote healthful behavior change. In this study, we aimed to describe participation and assessment results for this program across a five-year period. Enrollment in the Healthy Champions program was open to private and public K-12 schools across Pennsylvania beginning in 2013. School staff completed an assessment that scored aspects of the wellness environment and was used to enroll schools in the program. Schools were awarded star status (0–5) based upon responses and provided a tailored response to improve ratings, and with re-enrollment, became a simple way for schools to track progress. From 2013 to 2018, 592 schools enrolled for at least one year, representing 58 out of 67 counties (87%) in Pennsylvania. Mean star status at baseline was 2.89 out of 5; however, schools enrolled for multiple years (51%) saw significant improvement in star status, independent of school size and rural/urban status.